LSU's forgettable season in which the Tigers failed to qualify for the NCAA national championship tournament on their way to a 19-14 season has also dented Simmons' value in the eyes of Nike and Adidas.
Simmons attended the school because his godfather David Patrick is the associate head coach at LSU and a close friend of former Melbourne Tigers player Dave Simmons, Ben's father.
Industry insiders have previously estimated Simmons could demand a shoe contract worth between $US50 million and $US100 million, however DePaula says Simmons struggles at LSU have taken the shine off his perception of being basketball's next superstar.
He told The Vertical Podcast with Woj, Simmons' expected sneaker deal could be worth as little as $US12 million.
The show's host Adrian Wojnarowski asked DePaula if Simmons' reputation as the next LeBron James has been shattered by his disappointing finish at LSU.
James signed a $90 million contract with Nike in his first year out of high school in 2003 and recently signed the richest shoe deal in NBA history reportedly worth more than $US500 million in a lifetime deal with the apparel giant.
"There was a perception coming into his freshman year at LSU that he might be a player who could command a monster NBA superstar deal as he walked into the league," Wojnarowski said.
"We aren't talking any more about Ben Simmons as the next LeBron - as a transcendent talent anymore. Has he cost himself money in how Nike looks at him?"
De Paula said Simmons was in a stronger position for contract negotiations before he stepped in the door at LSU.
"I think it's totally fair to frame it that way," he said. "I think if you look maybe a year before he went to LSU, he was the guy. He was tabbed as the next guy for sure.
"People were all looking forward to the summer to sign him potentially. Between Adidas and Nike, they were both extremely hot on him. Maybe that meant a shoe deal in the range of $US50 million as a rookie, which is fairly unheard of.
"That's only once every five to seven years that happens for a guy like a (Kevin) Durant or LeBron style of player.
"I think now more realistically, you could be looking at the $US12 million to $US20 million range over that same period of time which is kind of more in line with the likes of Andrew Wiggins, John Wall and some of those other top picks of recent times have gotten. But not at all the kind of monster, transcendent deal you thought he was going to be."
DePaula believes Simmons also has some personal traits that would make Nike and Adidas nervous about offering a monster deal.
"There's just stretches of indifference for him," he said. "I think if you're a brand that's a red flag you're nervous about.
"A guy that's going to be engaged at all times and also a guy that's going to be excited to promote and talk about the brand that he's partnering with or is he going to be someone who goes through the motions at times.
"I think that element is tough. The other element that's tough right now as it stands is that he's trying to get the deal done before the draft, so it's not going to affect which market it ends up being drafted to.
"He's just having Nike and Adidas right now going head to head in negotiations. I don't know if he has enough leverage to pull off the deal that he was originally hoping for."
His potential slide to the No. 2 draft pick would also cost Simmons more than $US2 million over the full four years of an NBA rookie contract as determined by the NBA Rookie Salary Scale included in the NBA's collective bargaining agreement (CBA) with players.
The NBA Rookie Salary Scale outlines the No. 1 draft pick at the 2016 NBA Draft will earn $US4,753,000 in his first season - however, it is common for players to negotiate up to 120% of the wage recommended in the NBA Rookie Salary Scale.
Assuming Simmons would previously have been picked at No. 1 and negotiated the full 120% of rookie wages outlined in the CBA, he stood to earn $US25,402,976 over a full four seasons in the NBA.
Rookie contracts for first-round drafted players in the NBA (the top 30 selections) are all standardised four-year deals with clauses in the team's favour to activate the third and fourth years.
If Simmons drops to the No. 2 pick he will earn $US23,017,978 million over four years. That's $US2,384,998 less than the $US25,402,976 for the No. 1 pick.
That means Simmons' decision to go to school at LSU may end up costing him more than NZ$44 million ($US38 million in a shoe deal and $US2.3 million in player wages).
Poor guy. He'll be crying himself to sleep on his bed of $100 notes when he looks back at that decision to play in Louisiana.
- news.com.au